Classifications

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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
  • C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
  • B01D69/14—Dynamic membranes
  • B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
  • B01D69/148—Organic/inorganic mixed matrix membranes
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
  • B01D71/02—Inorganic material
  • B01D71/024—Oxides
  • B01D71/027—Silicium oxide
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
  • B01D71/06—Organic material
  • B01D71/30—Polyalkenyl halides
  • B01D71/32—Polyalkenyl halides containing fluorine atoms
  • B01D71/34—Polyvinylidene fluoride
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  • C03—GLASS; MINERAL OR SLAG WOOL
  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
  • C03C17/006—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character
  • C03C17/008—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character comprising a mixture of materials covered by two or more of the groups C03C17/02, C03C17/06, C03C17/22 and C03C17/28
  • C03C17/009—Mixtures of organic and inorganic materials, e.g. ormosils and ormocers
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  • C03—GLASS; MINERAL OR SLAG WOOL
  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
  • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
  • C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins
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  • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
  • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
  • C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
  • C03C17/42—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating of an organic material and at least one non-metal coating
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  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
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  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
  • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
  • C04B41/48—Macromolecular compounds
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  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
  • C04B41/81—Coating or impregnation
  • C04B41/82—Coating or impregnation with organic materials
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  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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  • C08J5/20—Manufacture of shaped structures of ion-exchange resins
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  • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
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  • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
  • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
  • C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
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  • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
  • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Definitions

• the invention pertains to certain fluoropolymer-based hybrid organic/inorganic composites with chemical bonds between the inorganic domains and the fluoropolymer phase, to a method for its manufacture, and to several uses and applications of the same.
• Organic-inorganic polymer hybrids wherein organic polymers are dispersed in inorganic solids on a nano or molecular level, have raised a great deal of scientific, technological and industrial interests because of their unique properties.
• TMOS tetramethoxysilane
• TEOS tetraethoxysilane
• the polymer can enhance the toughness and processability of otherwise brittle inorganic materials, wherein the inorganic network can enhance scratch resistance, mechanical properties, and surface characteristics of said hybrid.
• Hybrids made from sol-gel technique starting from fluoropolymers, in particular from vinylidene fluoride polymers are known in the art.
• PVDF Poly(vinylidene fluoride)
• Silica Hybrods having interpenetrating polymer network structure by using crystallization between PVDF chains.
• A J. polym. sci., A, Polym. chem. 2005, vol. 43, p. 3543-3550. discloses the synthesis of certain PVDF/silica hybrids by reacting a solution in DMF and gamma-butirolactone of PVDF with TMOS in the presence of a catalytic amount of HCl.
• U.S. Pat. No. 6,620,516 (ASAHI KASEI KK) 16/03/2003 discloses an organic domain/inorganic domain hybrid material wherein the organic domain comprises a water-soluble or water-dispersible organic polymer having a plurality of carboxylic acid groups, and the organic domain and the inorganic domain being ionically bonded to each other through the carboxylic groups of the organic polymer to form an ionically crosslinked structure.
• These hybrids are manufactured by reaction between the organic polymer as above detailed and certain metasilicate anions in an aqueous medium under basic conditions in the presence of certain divalent metal cations which will ensure the formation of the ionic network through simultaneous ionic chemical bond to the carboxylate and silicate groups.
• U.S. Pat. No. 7,244,797 (ASAHI KASEI KK) Jul. 17, 2007 discloses a similar approach, wherein, in addition, the organic polymer can comprise cationic functionalities (e.g. quaternary ammonium groups) which are ionically bound to the metasilicate function of the inorganic domain.
• cationic functionalities e.g. quaternary ammonium groups
• EP 1389634 A (DAIKIN INDUSTRIES LTD) Feb. 18, 2004 discloses a surface-treatment agent comprising:
• a hydrolyzable metal alkoxyde which can be notably TEOS;
• compound b) is a perfluoropolyether comprising functional groups of formula:
• Y is H or lower alkyl group; m and n is from 0 to 2; R1 is a hydrolysable group or a chlorine atom; R2 is a hydrogen atom or a inert monovalent group, M is a metal or a reactive group selected from the group consisting of an isocyanate group, a carboxyl group, a hydroxyl group, a glycidyl group, a phosphate group, an amino group, and a sulfonate group.
• the invention thus provides a process for manufacturing a fluoropolymer hybrid organic/inorganic composite [polymer (F-h)] comprising fluoropolymer domains and inorganic domains, said process comprising:
• At least one fluoropolymer [polymer (F)] comprising:
• each of R1, R2, R3, equal or different from each other is independently a hydrogen atom or a C 1 -C 3 hydrocarbon group, and R OH is a C 1 -C 5 hydrocarbon moiety comprising at least one hydroxyl group, and
• m is an integer from 1 to 4
• A is a metal selected from the group consisting of Si, Ti and Zr
• Y is a hydrolysable group
• X is a hydrocarbon group, optionally comprising one or more functional groups
• fluoropolymer domains derives from polymer (F) and the inorganic domains derives from compound (M), and
• inorganic domains are grafted to the fluoropolymer domains through reaction of at least a fraction of the ROH groups of the monomer (MA) with at least a fraction of the hydrolysable groups Y of compound (M);
• the invention pertains to a fluoropolymer hybrid organic/inorganic composite [polymer (F-h)] comprising inorganic domains, said hybrid being obtained by reaction between:
• inorganic domains are grafted to the polymer (F) through reaction of at least a fraction of the R OH groups of the monomer (MA) with at least a fraction of compound (M).
• fluoropolymer hybrid organic/inorganic composites of the present invention exhibit improved properties, in particular, with regards to adhesion to glass or ceramic materials, and/or with regards to their enhanced scratch resistance. Also, when a compound (M) is used, fluoropolymer hybrid organic/inorganic composites are obtained which can exhibit functional behaviour, for instance in terms of hydrophilicity or ion conductivity.
• the polymer (F) is a fluoropolymer comprising recurring units derived from at least one fluorinated monomer [monomer (FM)] and recurring units derived from at least one (meth)acrylic monomer [monomer (MA)].
• fluorinated monomer it is hereby intended to denote an ethylenically unsaturated monomer comprising at least one fluorine atom.
• fluorinated monomer is understood to mean that the polymer (F) may comprise recurring units derived from one or more than one fluorinated monomers.
• fluorinated monomers is understood, for the purposes of the present invention, both in the plural and the singular, that is to say that they denote both one or more than one fluorinated monomers as defined above.
• the term “at least one (meth)acrylic monomer [monomer (MA)]” is understood to mean that the polymer (F) may comprise recurring units derived from one or more than one(meth)acrylic monomers.
• the expression “(meth)acrylic monomers” is understood, for the purposes of the present invention, both in the plural and the singular, that is to say that they denote both one or more than one (meth)acrylic monomers as defined above.
• fluorinated monomer comprise at least one hydrogen atom, it is designated as hydrogen-containing fluorinated monomer.
• the fluorinated monomer (FM) may further comprise one or more other halogen atoms (Cl, Br, I).
• Non-limiting examples of suitable fluorinated monomers include, notably, the followings:
• the polymer (F) is advantageously a random polymer [polymer (F R )] comprising linear sequences of randomly distributed recurring units derived from at least one fluorinated monomer (FM) at least one monomer (MA).
• randomly distributed recurring units is intended to denote the percent ratio between the average number of sequences of at least one monomer (MA), said sequences being comprised between two recurring units derived from at least one fluorinated monomer, and the total average number of recurring units derived from at least one monomer (MA).
• the average number of sequences of at least one monomer (MA) equals the average total number of recurring units derived from at least one monomer (MA), so that the fraction of randomly distributed recurring units derived from at least one monomer (MA) is 100%: this value corresponds to a perfectly random distribution of recurring units derived from at least one monomer (MA).
• the polymer (F) may further optionally comprise recurring units derived from at least one hydrogenated monomer, different from the monomer (MA).
• hydrophilic monomer it is hereby intended to denote an ethylenically unsaturated monomer comprising at least one hydrogen atom and free from fluorine atoms.
• the term “at least one hydrogenated monomer” is understood to mean that the polymer (F) may comprise recurring units derived from one or more than one hydrogenated monomers.
• the expression “hydrogenated monomers” is understood, for the purposes of the present invention, both in the plural and the singular, that is to say that they denote either one or more than one hydrogenated monomers as defined above.
• the polymer (F) may be amorphous or semi-crystalline.
• amorphous is hereby intended to denote a polymer (F) having a heat of fusion of less than 5 J/g, preferably of less than 3 J/g, more preferably of less than 2 J/g, as measured according to ASTM D-3418-08.
• polysemi-crystalline is hereby intended to denote a polymer (F) having a heat of fusion of from 10 to 90 J/g, preferably of from 30 to 60 J/g, more preferably of from 35 to 55 J/g, as measured according to ASTM D3418-08.
• the polymer (F) is preferably semi-crystalline.
• the polymer (F) comprises preferably at least 0.01% by moles, more preferably at least 0.05% by moles, even more preferably at least 0.1% by moles of recurring units derived from at least one monomer (MA).
• the polymer (F) comprises preferably at most 10% by moles, more preferably at most 5% by moles, even more preferably at most 3% by moles of recurring units derived from at least one monomer (MA).
• Determination of average mole percentage of recurring units derived from at least one monomer (MA)] in the polymer (F) can be performed by any suitable method. Mention can be notably made of acid-base titration methods or NMR methods.
• the polymer (F) is preferably a partially fluorinated fluoropolymer.
• partially fluorinated fluoropolymer is intended to denote a polymer comprising recurring units derived from at least one fluorinated monomer (FM) and recurring units derived from at least one monomer (MA), wherein the fluorinated monomer (FM) comprises at least one hydrogen atom.
• the polymer (F) is preferably a partially fluorinated fluoropolymer comprising recurring units derived from vinylidene fluoride (VDF), at least one monomer (MA) and at least one fluorinated monomer [monomer (FM2)] different from VDF.
• VDF vinylidene fluoride
• MA monomer
• FM2 fluorinated monomer
• the polymer (F) of this first embodiment of the invention more preferably comprises recurring units derived from:
• Non limitative examples of monomer (MA) comprising at least one hydroxyl end group include, notably, hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate, hydroxyethylhexyl(meth)acrylate.
• the monomer (MA) is preferably selected from the followings:
• polymer (F) is a VDF/HEA/HFP terpolymer.
• the polymer (F) is typically obtainable by polymerization of at least one fluorinated monomer, at least one monomer (MA) as above defined, and, optionally, a monomer (FM2).
• the polymer (F) is typically obtainable by emulsion polymerization or suspension polymerization.
• the intrinsic viscosity of polymer (F), measured in dimethylformamide at 25° C. is lower than 0.50 l/g, more preferably lower than 0.45 l/g.
• the polymer (F-h) typically comprises, preferably consists of, fluoropolymer domains and inorganic domains.
• the selection of the hydrolysable group Y of the compound (M) of formula (I) as defined above is not particularly limited, provided that it enables under appropriate conditions the formation of a —O-A ⁇ bond between A of the compound (M) and the —O— atom belonging to the hydroxyl group on the R OH (meth)acrylic monomer (MA).
• the hydrolysable group Y of the compound (M) as defined above is typically selected from the group consisting of halogen atoms, preferably being a chlorine atom, hydrocarboxy groups, acyloxy groups and hydroxyl groups.
• X in compound (M) is R A and Y is OR B , wherein R A and R B , equal to or different from each other and at each occurrence, are independently selected from C 1 -C 18 hydrocarbon groups, wherein R A optionally comprises at least one functional group.
• the compound (M) as defined above comprises at least one functional group on X, it will be designated as functional compound (M1); in case none of X of the compound (M) as defined above comprise a functional group, the compound (M) will be designated as non-functional compound (M2).
• Non-limiting examples of functional groups that can be on X include, notably, epoxy group, carboxylic acid group (in its acid, ester, amide, anhydride, salt or halide form), sulphonic group (in its acid, ester, salt or halide form), hydroxyl group, phosphoric acid group (in its acid, ester, salt, or halide form), thiol group, amine group, quaternary ammonium group, ethylenically unsaturated group (like vinyl group), cyano group, urea group, organo-silane group, aromatic group.
• compound (M) is the compound (M1) wherein m is an integer from 1 to 3, A is a metal selected from the group consisting of Si, Ti and Zr, X is R A′ and Y is OR B′ , wherein R A′ is a C 1 -C 12 hydrocarbon group comprising at least one functional group and R B′ is a C 1 -C 5 linear or branched alkyl group, preferably R B′ being a methyl or ethyl group.
• Examples of functional compounds (M1) are notably vinyltriethoxysilane, vinyltrimethoxysilane, vinyltrismethoxyethoxysilane of formula CH 2 ⁇ CHSi(OC 2 H 4 OCH 3 ) 3 , 2-(3,4-epoxycyclohexylethyltrimethoxysilane) of formula:
• non-functional compounds are notably trimethoxysilane, triethoxysilane, tetramethoxysilane, tetraethoxysilane (TEOS), tetramethyltitanate, tetraethyltitanate, tetra-n-propyltitanate, tetraisopropyltitanate, tetra-n-butyltitanate, tetra-isobutyl titanate, tetra-tert-butyl titanate, tetra-n-pentyltitanate, tetra-n-hexyltitanate, tetraisooctyltitanate, tetra-n-lauryl titanate, tetraethylzirconate, tetra-n-propylzirconate, tetraisopropylzirconate, tetra-
• X in compound (M) is a C 1 -C 12 hydrocarbon group comprising at least one —N ⁇ C ⁇ O functional group and wherein A and Y are as above defined; in this case, compound (M) will be designated compound (M′).
• Y is OR D , wherein R D is a C 1 -C 5 linear or branched alkyl group, preferably R D being a methyl or ethyl group.
• Non-limiting examples of suitable compounds (M′) according to this embodiment include the followings: trimethoxysilyl methyl isocyanate, triethoxysilyl methyl isocyanate, trimethoxysilyl ethyl isocyanate, triethoxysilyl ethyl isocyanate, trimethoxysilyl propyl isocyanate, triethoxysilyl propyl isocyanate, trimethoxysilyl butyl isocyanate, triethoxysilyl butyl isocyanate, trimethoxysilyl pentyl isocyanate, triethoxysilyl pentyl isocyanate, trimethoxysilyl hexyl isocyanate and triethoxysilyl hexyl isocyanate.
• the at least one polymer (F-h) comprised in the membrane of the invention is obtained by reaction between:
• functional group of compound (M) will be preferably selected among carboxylic acid group (in its acid, ester, amide, anhydride, salt or halide form), sulphonic group (in its acid, ester, salt or halide form), hydroxyl group, phosphoric acid group (in its acid, ester, salt, or halide form), amine group, and quaternary ammonium group; most preferred will be carboxylic acid group (in its acid, ester, amide, anhydride, salt or halide form) and sulphonic group (in its acid, ester, salt or halide form).
• the compound (M) preferably complies with formula:
• m* is an integer from 2 to 3
• E* is a metal selected from the group consisting of Si, Ti and Zr
• R A equal to or different from each other at each occurrence, is a C 1 -C 12 hydrocarbon group, optionally comprising one or more functional group
• R B equal to or different from each other at each occurrence, is a C 1 -C 5 linear or branched alkyl radical, preferably R B is methyl or ethyl.
• the process of the invention comprises reacting at least a fraction of hydroxyl groups of R OH groups of said monomer (MA) of said polymer (F) with at least a fraction of said compound (M), so as to obtain a grafted polymer comprising pendant —Y m-1 AX 4-m groups, with m, Y, A and X having same meaning as above detailed.
• —OH groups of the R OH functionalities of monomer (MA) are able to react with the hydrolysable group(s) of the compound (M) so as to yield a covalent bond between the compound (M) moiety and the monomer (MA) moiety.
• Polymer (F) and compound (M) can be notably reacted in the molten state; melt compounders such as extruders, melt kneaders or other devices can be advantageously used to this aim.
• Polymer (F) and compound (M) can be also notably reacted in solution; according to this embodiment polymer (F) and compound (M) are at least partially dissolved in a solvent. Dissolution can be obtained either at room temperature or upon heating. The selection of this solvent is not critical, provided that it efficiently solvates both polymer (F) and compound (M) and does not interfere with the reaction between the hydroxyl groups of polymer (F) and the hydrolysable groups of compound (M).
• polar aprotic solvent will be preferably selected.
• these solvents mention can be notably made of N,N-dimethylformamide (DMF), N,N-dimethylacetamide, tetramethylurea, dimethylsulfoxide (DMSO), triethylphosphate, N-methyl-2-pyrrolidone (NMP), acetone, tetrahydrofuran, methylethylketone (MEK), methylisobutylketone (MIBK), glycol diethers, glycol ether-esters, n-butylacetate, cyclohexanone, diisobutylketone, butyrolactone, isophorone, propylene carbonate, glyceryl triacetate, dimethyl phthalate.
• DMF N,N-dimethylformamide
• DMSO dimethylsulfoxide
• NMP N-methyl-2-pyrrolidone
• MEK methylethylketone
• MIBK
• the mixture can further comprise, in addition to compound (M) and polymer (F), at least one inorganic filler.
• the inorganic filler is generally provided in the mixture under the form of particles.
• the inorganic filler particles generally have an average particles size of 0.001 ⁇ m to 1000 ⁇ m, preferably of 0.01 ⁇ m to 800 ⁇ m, more preferably of 0.03 ⁇ m to 500 ⁇ m.
• inorganic filler is not particularly limited; nevertheless, inorganic fillers having on their surface reactive groups towards compound (M) are generally preferred.
• reaction between at least a fraction of compound (M) with at least a fraction of said surface reactive group of the inorganic filler can occur simultaneously with the reaction of at least a fraction of compound (M) with at least a fraction of the ROH groups of the monomer (MA), so that in subsequent hydrolysis/polycondensation step, chemical bonding between the polymer (F) and the inorganic filler is likely achieved through the inorganic domains derived from compound (M).
• inorganic fillers suitable for being used in the process of the invention mention can be made of inorganic oxides, including mixed oxydes, metal sulphates, metal carbonates, metal sulfides and the like.
• metal oxides mention can be made of SiO 2 , TiO 2 , ZnO, Al 2 O 3 .
• a class of compounds which gave particularly good results within the context of this embodiment of the present invention are notably silicates, aluminium-silicates and magnesium silicates, all optionally containing additional metals such as sodium, potassium, iron or lithium.
• silicates aluminium-silicates and magnesium silicates are generally known as possessing a layered structure.
• silicates, aluminium-silicates and magnesium silicates all optionally containing additional metals such as sodium, potassium, iron or lithium can be notably smectic clays, possibly of natural origin, such as notably montmorillonites, sauconite, vermiculite, hectorite, saponite, nontronite.
• silicates, aluminium-silicates and magnesium silicates, all optionally containing additional metals such as sodium, potassium, iron or lithium can be selected among synthetic clays, like notably fluorohectorite, hectorite, laponite.
• particles of layered silicates, aluminium-silicates and magnesium silicates as above described having at least one dimension of less than 100 nm, preferably of less than 50 nm, more preferably of less than 10 nm.
• fluoropolymer hybrid organic/inorganic composites of the invention comprise said inorganic fillers.
• Said inorganic fillers are typically comprised in the inorganic domains of the composite of the invention.
• the process further comprises hydrolyzing and/or polycondensing compound (M) and/or pendant —Y m-1 AX 4-m groups, as above detailed to yield a fluoropolymer hybrid organic/inorganic composite comprising inorganic domains.
• the hydrolysis/polycondensation can be carried out simultaneously to the step of reacting hydroxyl groups of polymer (F) and compound (M) or can be carried out once said reaction has occurred.
• this hydrolysis/polycondensation is initiated by addition of appropriate catalyst/reactant.
• catalyst/reactant Generally, water or a mixture of water and an acid can be used for promoting this reaction.
• the choice of the acid is not particularly limited; both organic and inorganic acids can be used.
• HCl is among the preferred acids which can be used in the process of the invention.
• temperatures will range from 150 to 250° C. as a function of the melting point of the polymer (F); in case of reaction in solution, temperatures will be selected having regards to the boiling point of the solvent. Generally temperatures between 50 and 150° C., preferably between 60° C. and 120° C. will be preferred.
• hydrolysable group(s) of the compound (M) will react so as to yield a hybrid composite comprising fluoropolymer domain (2) consisting of chains of polymer (F) and inorganic domains (1) consisting of residues derived from compound (M).
• the fluoropolymer hybrid organic/inorganic composite comprising inorganic domains can be recovered from standard methods, which will depend upon techniques used in various reaction steps.
• the fluoropolymer hybrid organic/inorganic composites of the present invention are used for the treatment of glass and/or ceramic materials.
• the invention pertains to the use of said composite comprising coating a glass and/or a ceramic surface with a layer comprising said composite.
• Said layer comprising the inventive composite can be used as aesthetic finish, in particular possibly in admixture with pigments or other fillers, or can be used as shatterproof coating.
• the composite of the invention can be used as a coating on different substrates for conferring scratch resistance. While the selection of materials which can be successfully coated with the composite of the invention is not particularly limited, it is generally understood that plastic materials will be preferred.
• composites of the present invention in particular those composites which are obtained by reaction between polymer (F) and a functional compound (M) can be used as raw materials for the manufacture of membranes for electrochemical applications and/or for separation processes.
• preferred composites for this use are those wherein the functional compound (M) used for their manufacture comprise a functional group selected from the group consisting of carboxylic acid group (in its acid, ester, amide, anhydride, salt or halide form), sulphonic group (in its acid, ester, salt or halide form), hydroxyl group, phosphoric acid group (in its acid, ester, salt, or halide form), amine group, and quaternary ammonium group; preferably from the group consisting of carboxylic acid group (in its acid, ester, amide, anhydride, salt or halide form) and sulphonic group (in its acid, ester, salt or halide form).
• inventive composites can be used for the manufacture of separators for Lithium
• composites of the present invention in particular those composites which are obtained by reaction between polymer (F) and a functional compound (M) can be used as electroluminescent materials in photovoltaic or organic light emitting devices.
• preferred composites for this use are those wherein the functional compound (M) used for their manufacture comprise a functional group having electro-optic properties, such as notably hole transport capabilities, electron transport capabilities, chromophores and the like.
• the functional compound (M) used for their manufacture comprise a functional group having electro-optic properties, such as notably hole transport capabilities, electron transport capabilities, chromophores and the like.
• these groups mention can be made of functional groups comprising carbazoles, oxadiazoles, tetraphenylenetetramine, dicyanomethylene-4-H-pyran, naphtalimide groups.
• composites of the present invention in the field of optics exploit combination of properties such as transparency, good adhesion, barrier properties, corrosion protection, easy tuning of refractive index, adjustable mechanical properties and decorative properties.
• composites of the present invention can be used for coating surfaces comprising superficial hydroxyl groups; in this case, application of the composite can be performed during the hydrolysis/polycondensation phase so as to have compound (M) possibly establishing a chemical bond with the surface to be coated.
• Cellulose-based surfaces can be notably used within this approach so as to yield corresponding coated surfaces comprising the composite of the invention.
• substrates suitable as substrates mention can be made of textiles, fabrics (e.g. for clothing), wood parts (′e.g. for furniture), paper (e.g. for packaging).
• Polymer 1-Comp VDF-HEA (0.8% by moles)-HFP (2.4% by mole) polymer having an intrinsic viscosity of 0.077 l/g in DMF at 25° C.
• VDF vinylidene fluoride
• HSA hydroxyethylacrylate
• HFP hexafluoropropylene
• VDF vinylidene fluoride
• the reactor was gradually heated until a set-point temperature at 55° C. and the pressure was fixed at 120 bar.
• the pressure was kept constantly equal to 120 bars by feeding 16.9 kg of aqueous solution containing 235 g of HEA during the polymerization. After this feeding, no more aqueous solution was introduced and the pressure started to decrease until 90 bar. Then, the polymerization was stopped by degassing the reactor until reaching atmospheric pressure. In general a conversion around 76% of monomers was obtained.
• the polymer so obtained was then recovered, washed with demineralised water and oven-dried at 65° C.
• the reactor was gradually heated until a set-point temperature at 48° C. and the pressure was fixed at 120 bar.
• the pressure was kept constantly equal to 120 bars by feeding 14.54 kg of aqueous solution containing at 4.55 g/kg of HEA in water during the polymerization. After this feeding, no more aqueous solution was introduced and the pressure started to decrease until 115 bar. Then, the polymerization was stopped by degassing the reactor until reaching atmospheric pressure. In general a conversion around 79% of comonomers was obtained.
• the polymer so obtained was then recovered, washed with demineralised water and oven-dried at 65° C.
• the reactor was gradually heated until a set-point temperature at 55° C. and the pressure was fixed at 120 bar.
• the pressure was kept constantly equal to 120 bars by feeding 834 g of aqueous solution containing 9 g of HEA. After this feeding, no more aqueous solution was introduced and the pressure started to decrease until 115 bar. Then, the polymerization was stopped by degassing the reactor until reaching atmospheric pressure. In general a conversion around 78% of comonomers was obtained.
• the polymer so obtained was then recovered, washed with demineralised water and oven-dried at 65° C.
• Hybrid Polymer/silica composite comprising 10% of silica
• Hybrid Polymer/silica composite comprising 20% of silica 2.5 grams of the polymer prepared according to any of examples 1 or 2 were dissolved in 22.5 grams of N-methylpyrrolidone (NMP). Then, 2.167 grams of TEOS were added drop-wise to the stirred solution, followed by 1.040 ml of aqueous HCl (0.1 M); the mixture was stirred at 60° C. for 2 hours to ensure the sol-gel reaction (TEOS hydrolysis and polycondensation) so as to obtain a clear solution of a hybrid VDF-HEA/silica composite.
• the silica content calculated assuming complete TEOS hydrolysis/polycondensation to SiO 2 , was 20% wt referred to the composite.
• the resulting films were smooth, homogeneous, and opaque.
• Wet Film thickness was about 500 ⁇ m.
• Dry Film thickness was about 25-35 ⁇ m.
• Adhesion among glass and hybrid composite film was determined according to ISO 2409 standard and according to ASTM D-3359. The results are shown in Table 2.

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